Réaction #47018

Équation de réaction

cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic acid, tert-butyl ester

intermediate 59

phenethylamine

→

product 93

Rendement 44.2%

2-(Phenethylamino)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole-1-carboxylic acid tert-butyl ester

Rendement 44.2%

Solvants

MeOH

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is cooled to RT
2. 2
   Autreis purified by chromatography on silica gel
3. 3
   Lavagegradient elution with heptane:EtOAc (75:25-60:40)

Mode opératoire

A mixture of intermediate 59 (2.0 g, 5.43 mmol), phenethylamine (2.04 mL, 16.3 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (75:25-60:40) gives 1.06 g of the product 93. 1H NMR (CDCl3) δ 7.40-7.30 (m, 4 H), 7.30-7.10 (m, 2 H), 7.10-6.90 (m, 8 H), 6.80-6.65 (m, 2 H), 5.45-5.25 (m, 2 H), 3.90-3.60 (m, 2 H), 3.05 (t, 2 H), 1.13 (s, 9 H); MS: m/z 442 (M++1).

Source